US10941087B2 - Process and plant for the adiabatic nitration of aromatic compounds - Google Patents

Process and plant for the adiabatic nitration of aromatic compounds Download PDF

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US10941087B2
US10941087B2 US16/483,483 US201716483483A US10941087B2 US 10941087 B2 US10941087 B2 US 10941087B2 US 201716483483 A US201716483483 A US 201716483483A US 10941087 B2 US10941087 B2 US 10941087B2
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organic compounds
aromatic organic
acid
nitrated
nitration
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US20200017421A1 (en
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Jürgen Pöhlmann
Heinrich Hermann
Mirko Händel
Sophie Wernitz
Stefan Fankel
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Josef Meissner GmbH and Co KG
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Josef Meissner GmbH and Co KG
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Assigned to JOSEF MEISSNER GMBH & CO. KG reassignment JOSEF MEISSNER GMBH & CO. KG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FANKEL, Stefan, HÄNDEL, DR. MIRKO, HERMANN, DR. HEINRICH, PÖHLMANN, DR. JÜRGEN, WERNITZ, Sophie
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0488—Flow sheets
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0053—Details of the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/18—Stationary reactors having moving elements inside
    • B01J19/1812—Tubular reactors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2415—Tubular reactors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2455—Stationary reactors without moving elements inside provoking a loop type movement of the reactants
    • B01J19/2465—Stationary reactors without moving elements inside provoking a loop type movement of the reactants externally, i.e. the mixture leaving the vessel and subsequently re-entering it
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B43/00—Formation or introduction of functional groups containing nitrogen
    • C07B43/02—Formation or introduction of functional groups containing nitrogen of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/16—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00477—Controlling the temperature by thermal insulation means
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/0015—Controlling the temperature by thermal insulation means
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/00479—Means for mixing reactants or products in the reaction vessels
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the formation of by-products can be greatly reduced by lowering the initial temperature and thus also the final temperature.
  • Each decrease in the initial temperature by 20 to 25° C. leads to a halving of the nitrophenol content in the crude nitrobenzene.
  • Lowering of the initial temperature from about 110° C. to about 80° C. leads to a reduction in the nitrophenol content by about 50%, i.e. to about 1500 ppm and less (e.g. 1000 ppm), compared to the circumstances described, for example, in EP 0 436 443 A2, particularly preferably to a value of about 1000 ppm.
  • the content of dinitrobenzene (DNB) decreases analogously to about 100 ppm (cf., for example, U.S. Pat. No. 8,692,035 B2 or WO 2010/051616 A1).
  • the nitration mixture can be converted to an extent of at least 98% at the prescribed reaction or residence time in the reactor.
  • benzene is used as nitratable aromatic organic compound (aromatic) and mononitrobenzene (MNB) is obtained as nitrated aromatic organic compound (nitroaromatic).
  • the three-step scrub usually comprises the following steps:
  • the amount of nitrated aromatic organic compounds (nitroaromatics) added and/or recirculated for the conversion and/or nitration reaction can also vary within a wide range.
  • the pressure drop per mixing element can, in particular, be from 0.1 bar to 3.0 bar, preferably from 0.3 to 1.5 bar, particularly preferably from 0.3 to 0.8 bar.
  • preference can be given to the mixing elements being arranged in the tube reactor in such a way that the conversion of the nitric acid of the nitric acid/sulfuric acid nitrating acid mixture is at least 40%, in particular at least 50%, preferably at least 60%, in the first 10 to 30% by volume of the reactor.
  • preference can likewise be given to the mixing elements being arranged in the tube reactor in such a way that the conversion of introduced nitric acid at the end of the tube reactor is at least 98%, preferably at least 99%, particularly preferably at least 99.5%.
  • the process or the conversion and/or nitration reaction can be carried out in a reactor, in particular tube reactor, wherein a dispersing device, preferably a mixing device, in particular for producing a dispersion or emulsion, in particular the starting reaction mixture or the nitration mixture, is located upstream of the reactor, in particular tube reactor.
  • a dispersing device preferably a mixing device, in particular for producing a dispersion or emulsion, in particular the starting reaction mixture or the nitration mixture
  • the dispersing device in particular the mixing device
  • the dispersing device in particular the mixing device
  • the dispersing device in particular the mixing device, can be configured as a pump, in particular a centrifugal pump.
  • the initial temperature is given by the mixing temperature of the individual feedstreams and in the case of an adiabatic nitration, in particular of benzene to give nitrobenzene, is typically in the range from 70 to 120° C., in particular in the range from 80 to 120° C., preferably in the range from 80 to 110° C., particularly preferably in the range from 85 to 105° C.
  • the initial temperature for the conversion and/or nitration reaction is not more than 120° C., in particular not more than 100° C., preferably not more than 95° C., particularly preferably not more than 90° C.
  • An efficient lowering of the interfacial tension between the organic phase and the acid phase is likewise achieved by admixing the benzene to be nitrated with nitrobenzene in such a way that a mixture of benzene/nitrobenzene comprising from 0.1 to 50%, preferably from 5.0 to 45%, particularly preferably from 11 to 40%, of nitrobenzene is introduced.
  • nitrated product e.g. nitrobenzene
  • product e.g. nitrobenzene
  • this scrubbing unit can typically comprise
  • FIG. 2 a - d further schematic depictions of various variants of the process of the invention or the production plant of the invention as per further preferred embodiments of the present invention ( FIGS. 2 b - c ) compared to the prior art ( FIG. 2 a );
  • FIG. 3 shows a further schematic depiction of the process of the invention or the inventive production plant according to the present invention as per a particular embodiment of the present invention: according to FIG. 3 , the nitration, in particular under adiabatic conditions, of the nitratable aromatic organic starting compounds (aromatics) to give the corresponding nitrated aromatic organic compounds (nitroaromatics) firstly occurs in a nitration unit N according to the above-described reaction approach (i.e. starting reaction mixture composed of aromatic to be nitrated and nitric acid/sulfuric acid nitrating acid mixture and addition of corresponding nitrated product).
  • a nitration unit N i.e. starting reaction mixture composed of aromatic to be nitrated and nitric acid/sulfuric acid nitrating acid mixture and addition of corresponding nitrated product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US16/483,483 2017-02-03 2017-12-14 Process and plant for the adiabatic nitration of aromatic compounds Active US10941087B2 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
DE102017000973 2017-02-03
DE102017000973.2 2017-02-03
DE102017106881.3 2017-03-30
DE102017106881 2017-03-30
DE102017110084.9A DE102017110084B4 (de) 2017-02-03 2017-05-10 Verfahren und Anlage zur adiabatischen Nitrierung von Aromaten
DE102017110084.9 2017-05-10
PCT/EP2017/082770 WO2018141451A1 (fr) 2017-02-03 2017-12-14 Procédé et installation de nitruration adiabatique de composés aromatiques

Publications (2)

Publication Number Publication Date
US20200017421A1 US20200017421A1 (en) 2020-01-16
US10941087B2 true US10941087B2 (en) 2021-03-09

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US16/483,483 Active US10941087B2 (en) 2017-02-03 2017-12-14 Process and plant for the adiabatic nitration of aromatic compounds

Country Status (12)

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US (1) US10941087B2 (fr)
EP (1) EP3555039B1 (fr)
JP (1) JP7519023B2 (fr)
KR (1) KR102214750B1 (fr)
CN (1) CN110546130B (fr)
CA (1) CA3052335C (fr)
DE (1) DE102017110084B4 (fr)
EA (1) EA201991832A1 (fr)
HU (1) HUE051426T2 (fr)
PL (1) PL3555039T3 (fr)
PT (1) PT3555039T (fr)
WO (1) WO2018141451A1 (fr)

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
DE102018217955B4 (de) * 2018-10-19 2020-06-04 Plinke Gmbh Verfahren zur Aufarbeitung von Mischsäure und Abwasser aus der Nitrierung von Aromaten sowie Vorrichtung zur Durchführung des Verfahrens
CN112707822B (zh) * 2020-12-30 2022-02-08 东营安诺其纺织材料有限公司 一种氯苯一步绝热连续硝化制备2,4-二硝基氯苯的方法
WO2024003050A1 (fr) 2022-06-28 2024-01-04 Basf Se Procédé de production de nitrobenzène
CN115466182B (zh) * 2022-09-05 2023-08-29 清华大学 一种高选择性合成间二硝基苯的方法

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EP0373966A2 (fr) 1988-12-15 1990-06-20 Chemetics International Company Ltd. Procédé de préparation de composés organiques nitrés
WO2014016292A1 (fr) 2012-07-27 2014-01-30 Bayer Materialscience Ag Procédé de preparation de nitrobenzène par nitrification adiabatique
US20150175522A1 (en) * 2012-07-27 2015-06-25 Bayer Materialscience Ag Method for producing nitrobenzene by adiabatic nitriding

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Publication number Publication date
CN110546130A (zh) 2019-12-06
KR20190115007A (ko) 2019-10-10
JP7519023B2 (ja) 2024-07-19
PT3555039T (pt) 2020-10-01
EP3555039B1 (fr) 2020-08-05
CA3052335A1 (fr) 2018-08-09
EP3555039A1 (fr) 2019-10-23
CN110546130B (zh) 2022-07-15
DE102017110084A1 (de) 2018-08-09
CA3052335C (fr) 2022-06-21
US20200017421A1 (en) 2020-01-16
KR102214750B1 (ko) 2021-02-10
JP2020506188A (ja) 2020-02-27
HUE051426T2 (hu) 2021-03-01
EA201991832A1 (ru) 2020-01-09
PL3555039T3 (pl) 2021-02-08
WO2018141451A1 (fr) 2018-08-09
DE102017110084B4 (de) 2019-07-04

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